An amine protecting group deprotectable under nearly neutral oxidative conditions
Document Type
Article
Publication Date
7-13-2018
Department
Department of Chemistry
Abstract
The 1,3-dithiane-based dM-Dmoc group was studied for the protection of amino groups. Protection was achieved under mild conditions for aliphatic amines, and under highly reactive conditions for the less reactive arylamines. Moderate to excellent yields were obtained. Deprotection was performed by oxidation followed by treating with a weak base. The yields were good to excellent. The new amino protecting group offers a different dimension of orthogonality in reference to the commonly used amino protecting groups in terms of deprotection conditions. It is expected to allow a collection of transformations to be carried out on the protected substrates that are unattainable using any known protecting groups.
Publication Title
Beilstein Journal of Organic Chemistry
Recommended Citation
Shahsavari, S.,
McNamara, C.,
Sylvester, M.,
Bromley, E.,
Joslin, S.,
Lu, B.,
&
Fang, S.
(2018).
An amine protecting group deprotectable under nearly neutral oxidative conditions.
Beilstein Journal of Organic Chemistry,
14, 1750-1757.
http://doi.org/10.3762/bjoc.14.149
Retrieved from: https://digitalcommons.mtu.edu/michigantech-p/15217